Sodium hydride → HCID 16658841, compound

HRID 990953Notes

Reaction equation

HRID 990953 reaction equation
F[C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[N:4]([CH2:10][C:11]([F:14])([F:13])[F:12])[C@H:5]([CH2:8][CH3:9])[CH2:6][OH:7].[H-].[Na+]>C1COCC1>[CH2:8]([C@H:5]1[N:4]([CH2:10][C:11]([F:14])([F:13])[F:12])[C:3]2[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:2]=2[O:7][CH2:6]1)[CH3:9]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 16659481HCID 16659481, compound

Product 1

HCID 16658841HCID 16658841, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

This compound was prepared according to General Method 20 from (2R )-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-1-butanol (5.4 g, 17.3 mmol) in 45 mL THF and NaH (1.4 g, 35 mmol) in 10 mL THF heated at reflux for 1 hr to afford 3.78 g (75%) of (3R)-3-ethyl-3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine, after flash chromatography (gradient elution, hexanes:ethyl acetate 95:5 to 50:50). Data for (3R)-3-ethyl-3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine: 1H NMR (500 MHz, CDCl3) δ 7.81 (dd, J=8.8, 2.4, 1H), 7.73 (d, J=2.9, 1H), 6.72 (d, J=8.8, 1H), 4.34 (dd, J=11.2, 1.5, 1H), 4.13 (m, 1H), 4.03 (dd, J=11.2, 2.4, 1H), 3.8 (m, 1H), 3.37 (m, 1H), 1.67 (m, 1H), 1.01 (t, J=7.3, 3H).

Workup

  1. customThis compound was prepared
  2. temperatureheated
  3. temperatureat reflux for 1 hr

Sources & evidence

ORD record
ord-3d80c68c5f6740398596497b2007fc2b
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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